(aminomethyl)(methyl)phosphinic acid | 15901-11-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (aminomethyl)(methyl)phosphinic acid
• 英文别名: (aminomethyl)-methylphosphinic acid；(aminomethyl)methylphosphinic acid；aminomethyl(methylphosphinic) acid；1-aminomethylphosphinic acid；aminomethylmethylphosphinic acid；α-Aminomethylmethylphosphinsaeure；Azaniumylmethyl(methyl)phosphinate
• CAS: 15901-11-8
• 化学式: C₂H₈NO₂P
• mdl: MFCD01317956
• 分子量: 109.065
• InChiKey: QLAUIXHXGPSZQW-UHFFFAOYSA-N

物化性质

• 熔点：
  296-298 °C(Solv: ethanol, 66% (64-17-5))
• 沸点：
  391.7±25.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2922499990

反应信息

• 作为反应物：
  描述：

  (aminomethyl)(methyl)phosphinic acid 、 N-苄氧羰基-L-丙氨酸 N-羟基琥珀酰亚胺酯 在 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 {[(N-benzyloxycarbonyl-L-alanyl)amino]methyl}-methylphosphinic acid
  参考文献：
  名称：

  Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid

  摘要：

  Phosphonodipeptides and phosphonooligopeptides based on L- and D-(1-aminoethyl)phosphonic acids L-Ala(P) and D-Ala(P) and (aminomethyl)phosphonic acid Gly(P) at the acid terminus have been synthesized and investigated as antibacterial agents, which owe their activity to the inhibition of bacterial cell-wall biosynthesis. A method for large-scale synthesis of the potent antibacterial agent L-Ala-L-Ala(P) (1, Alafosfalin) is described. Structure-activity relationships in the dipeptide series have been studied by systematic variation of structure 1. L stereochemistry is generally required for both components. Changes in the L-Ala(P) moiety mostly lead to loss of antibacterial activity, but the phosphonate analogues of L-phenylalanine, L-Phe(P), and L-serine, L-Ser(P), give rise to weakly active L-Ala-L-Phe(P) and L-Ala-L-Ser(P). Replacement of L-Ala in 1 by common and rare amino acids can give rise to more potent in vitro antibacterials such as L-Nva-L-Ala(P) (45). Synthetic variation of these more potent dipeptides leads to decreased activity. Phosphonooligopeptides such as (L-Ala)2-L-Ala(P) have a broader in vitro antibacterial spectrum than their phosphonodipeptide precursor, but this is not expressed in vivo, presumably due to rapid metabolism to 1. Stabilized compounds such as Sar-L-Nva-L-Nva-L-Ala(P) (46) have been developed that are more potent in vivo and have a broader in vivo antibacterial spectrum than the parent phosphonodipeptide.

  DOI：

  10.1021/jm00151a005
• 作为产物：
  描述：

  (acetylaminomethyl)(methyl)phosphinic acid ethyl ester 在 盐酸 作用下， 以94%的产率得到(aminomethyl)(methyl)phosphinic acid
  参考文献：
  名称：

  Natchev, Ivan A., Liebigs Annalen der Chemie, 1988, p. 861 - 868

  摘要：

  DOI：

文献信息

• A Convenient One-Pot Preparation of Disubstituted Phosphinic Acids Derived from Simple Amino Acids and Proline
  作者：Marianne Borloo、Xian-Yun Jiao、Halina Wójtowicz、Padinchare Rajan、Christophe Verbruggen、Koen Augustyns、Achiel Haemers

  DOI：10.1055/s-1995-4050

  日期：1995.9

  A facile method for the preparation of both 2-pyrrolidinyl-substituted phosphinic acids and 1-aminoalkylphosphinic acids is described. Reaction of 1-pyrroline trimer or N-tritylalkanamine with bis(trimethylsilyl)phosphonite, followed by silylation with N,O-bis(trimethylsilyl)acetamide gives an intermediate which is used in a Michael addition reaction or an Arbuzov reaction.

  本文介绍了一种制备 2-吡咯烷基取代的膦酸和 1-氨基烷基膦酸的简便方法。先将 1-吡咯啉三聚体或 N-三苯甲基烷胺与双（三甲基硅基）亚磷酸反应，然后用 N,O-双（三甲基硅基）乙酰胺进行硅烷化反应，得到一种中间体，可用于迈克尔加成反应或阿尔布佐夫反应。
• Phosphonic acid and phosphinic acid tripeptides as inhibitors of glutathionylspermidine synthetase
  作者：Christophe Verbruggen、Sofie De Craecker、Padinchare Rajan、Xian-Yun Jiao、Marianne Borloo、Keith Smith、Alan H. Fairlamb、Achiel Haemers

  DOI：10.1016/0960-894x(96)00001-7

  日期：1996.2

  A series of phosphonic and phosphinic acid derivatives of glutathione were synthesized as potential inhibitors of glutathionylspermidine synthetase, an essential enzyme in the biosynthesis of trypanothione in trypanosomatids. The compounds showed moderate activity.
• Maier, Ludwig, Phosphorus and Sulfur and the Related Elements, 1983, vol. 14, p. 295 - 322
  作者：Maier, Ludwig

  DOI：——

  日期：——
• CH624965
  申请人：——

  公开号：——

  公开（公告）日：——
• Oleksyszyn,J. et al., Polish Journal of Chemistry, 1979, vol. 53, p. 1347 - 1349
  作者：Oleksyszyn,J. et al.

  DOI：——

  日期：——